Lessons Learned as a Founder and CEO

When I started Afolio, I had no idea just how transformative this journey would be, and once I jumped in, I never looked back.  The experience of starting something new, finding great people that shared my values and vision, and working together to create something different, useful and fun is something I will remember forever.  I wrapped up my company, after almost six years of building it, and realized that I learned a tremendous amount – about being a CEO, building products, leading people, and about who I am.

It was the closing of one chapter, and the beginning of a new one.  I’ve had some time to reflect on what I’ve learned and it’s a lot.  It’s hard to condense almost six years of learning and doing, but here are 8 key lessons I learned that I hope to carry with me next time around:

1. Invest in people and building relationships.

People are and always will be your strongest asset in your company.  Make sure you have a clear idea of what your values are and recruit people that fit your culture.  Also, be willing to pay great people more if they ask for it.  Really good people are worth every penny. Invest in them and you’ll be surprised at what they can do.

Keep them happy by making sure you actively listen to them, communicate with them, challenge them with their work, and treat them with respect.

Investing in people and building relationships not only applies to your employees, but also to your strategic partners and potential customers.  You shouldn’t start developing relationships with people when you need them, but when you don’t.  Just like relationships with your spouse or partner, it takes time and energy to cultivate a relationship and the same is true for business partners.  It takes time to build trust and rapport with someone.  Who knows, perhaps they may be a potential acquirer in the future.

Relationships nurture your soul, so surround yourself with people you respect and enjoy being with, not just in your work life, but in your personal life as well.  Don’t neglect the important people in your life.  Make time to continue developing the relationships that matter and you’ll be happy you did.

2. Importance of a strong support network.

People often say that it takes a village to raise a child, and the same is true for building a company.  You just can’t deal with everything on your own.  It’s lonely, mentally grueling, emotionally taxing, and hard building a company.  And let’s face it, it’s even harder when you are a new parent.  You need all the help you can get, whether it comes in the form of a co-founder, a supportive spouse, a parent, a close friend, or an entrepreneur support group.  These people will help you in ways you can’t even imagine.  To your employees, investors, and board members, you always have to take on the role of CEO and sometimes that can be exhausting.

Finding people to talk with that aren’t direct stakeholders in your company can be a healthy outlet.  My husband ended up being an important part of my support network.  Since I was an entrepreneur and a mother, I was lucky to have a husband who was not only a fellow entrepreneur, but he was also a hands-on father and helped balance the load at home when it got too heavy.

Having a great CEO coach can also be very helpful.  You wouldn’t train for the Olympics without a strong coach, so why would you train to be a world class CEO without one?   Surround yourself with people you can trust and talk with them openly.

3. Plan for the future, but adapt for the present.

You might think this doesn’t make sense for an early stage entrepreneur but it does.  Planning for the future means setting goals and identifying milestones along the way to help you stay on track to reach your goals.  If you don’t plan in advance, things just won’t get done.  Bigger companies are much more disciplined about this than early stage startups, and I think that’s unfortunate.  Even 3-5 people startups should plan.  Make 30-60-90 day plans, then make 6 and 12 month plans.  Then when you’re bigger, plan for five years out.  You wouldn’t start building a house without some type of blueprint would you?  Long term thinking CEOs win out in the end.  Jeff Bezos of Amazon wouldn’t have built Amazon to what it is today without thinking long term.  As Bezos says, thinking long term is a competitive advantage.
Planning for the future also means anticipating the possible risks you might encounter along the way.  Just identifying what those might be in advance helps you act more nimbly when you need to.
Adapting for the present means that if you’ve thought about the long term and you hit a bump along the way, adjust your approach as needed and move on.

4. Focus. Focus. Focus.

After you’ve planned for the future, you need to focus on the present.  And the best way to focus on the present is to control your calendar.  That means being ruthless about how you spend your time – who you meet with, where you go, and what you have meetings about.  You should not attend meetings if there isn’t a clear purpose and desired outcome for the meeting.  This has two benefits.  First, it allows you to focus your time on what’s most important, not just urgent, and second, it sets an excellent example for your team.  It shows your team that every person’s time is valuable, so don’t waste yours or anyone else’s time.  Time is one of your most precious resources, so treat it accordingly.

Focus also means, once you’ve identified what needs to be done, focus your time and resources solely on that.  Always ask yourself, will what I’m doing now help me make progress on my current goal?  If the answer is ever ‘No’, then stop doing it.  Distractions are your worst enemy.  Stay laser focused and make sure your team does as well.

5. Trust your gut.

Even with all the talk about data, analytics, etc driving decisions, when you’re running a company, information comes at you in many different forms and your gut is the best equipped to process it all, and help you make the best decision.  If you like reading the science behind this, read this. I’ve found that decisions I’ve made with my gut more often than not turn out to be right, especially when making decisions about hiring, and firing. You may often feel that you need to justify your decisions based on data and getting as much information as possible, but making a key decision based on your instinct rarely backfires.  Just be sure that you’re being honest and forthright when you’re using your gut.

6. Become a better storyteller.

A lot of your job as CEO is being an effective communicator, and being able to tell compelling stories is crucial.  It helps you recruit amazing employees and convince them of your vision, it helps you raise money when you need it, it helps you inspire your team, and it makes you a better overall communicator.  Humans relate to stories.  That’s how information has been passed down before there were books.  Great storytellers know how to draw you in, make you believe, and tell things in rich detail.  How do you become a better storyteller?  Practice.  Find opportunities where you have to tell a story about your company and get a reaction.  Put yourself in your audience’s shoes.  Would you find your story compelling?

7. Be growth minded.

Just like in competitive athletics, a lot of your success as a CEO comes down to your mental toughness.  Carol Dweck wrote an incredible book called Mindset, and if you haven’t read it yet, you should.  Being growth minded is a life approach and it allows you to deal with adversity and to view obstacles not as setbacks, but as opportunities to learn and grow. There were times with my company when I just wanted to curl up into a ball or just throw my hands up and give up, but when I reminded myself that I’m in control of how I react to a situation, it gave me the freedom to see new solutions and get through whatever I was facing.  I won’t lie and tell you that having a growth mindset is always easy, but when you do it regularly, you get better at it and it becomes more of a habit.  Plus, it just makes you happier.

8. Keep learning.

If you’ve decided to be an entrepreneur and start your own company, you’ll be learning constantly, and it shouldn’t ever stop.  Although learning isn’t just about learning more about your customers and your industry (which is important), it also means pushing yourself to learn more about things going on in your world.  In our world.  Learn something you know nothing about.  Knowledge is yours for the taking.  Sometimes when you’re learning something else, your subconscious solves a previously unsolvable problem for you behind the scenes.  I know that as an entrepreneur, your time is very limited, but I wish I’d read a lot more while I was running my company.  Books expand your thinking and give you new perspectives to consider.

Two books that I recently read that I really enjoyed were The Organized Mind and The Power of Habit.  I love neuroscience and understanding why people do what they do, as well as improving myself and both these books deliver on these fronts.  I also finished reading From Shanghai To Silicon Valley, written by an entrepreneur who was a CEO for over 30 years, which was also excellent.

I hope these hard learned lessons can benefit you if you’re an entrepreneur trying to build your business.  It’s an exhilarating, frustrating, challenging and rewarding experience, and let me tell you, you can do it!

I was really fortunate when I ran my company to have other entrepreneurs share great advice with me and helped me when I needed them, and I want to pay it forward.  No matter what I do next, I believe strongly in helping the community I’m a part of.

I hope to continue learning and would love to hear your feedback in the comments.

Thank you for reading and keep learning!


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